Deals on vacations and trips to Cumberland County

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Portland Head Light showing rocky coastline, general coastal views and a sunset

Portland

Vacations
Portland

Cumberland County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Porter Square Hotel

Porter Square Hotel

3 out of 5
Porter Square
Save 100% on your flight
Price was $368, price is now $256 per person
$256
per person
Feb 5 - Feb 8
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A garden, express check-out, and a computer station are also on offer.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,386, price is now $939 per person
$939
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $1,621, price is now $1,157 per person
$1,157
per person
Mar 13 - Mar 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
This smoke-free hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the laundry service, conference space, and valet parking. A lobby fireplace, luggage storage, and concierge services are also on offer.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,149, price is now $825 per person
$825
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $851, price is now $626 per person
$626
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.

Top Cumberland County hotels deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $93 total per night
$93 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.
Pool
Hot Tub
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $98 total per night
$98 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Spa
Pet friendly
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $165 total per night
$165 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.
Hot Tub
Spa
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $163 total per night
$163 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Pet friendly
Free WiFi
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $135 total per night
$135 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Free WiFi
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Free Cancellation
$78 nightly
The price is $86 total per night
$86 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.
Pool
Free airport shuttle
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Photos of local treasures

Browse Cumberland County vacation photos for more inspiration

Freeport featuring signage
Portland which includes a garden
Portland featuring a park
Portland showing a bay or harbor
Portland which includes fall colors

Frequently asked questions

How much are vacation packages to Cumberland County?
$256 is all you'll need for a memorable break in Cumberland County. Bundle your flights and hotel into a Travelocity package and see how much the savings pile up. With such good prices, you'll want to start packing your bags now!
Where can I get the best vacation package deals for Cumberland County?
Look no further than Travelocity. With as many as 400 airlines and 1,000,000 properties across the globe, it's a breeze to find a Cumberland County package deal that satisfies your wanderlust.
Why should I purchase my Cumberland County vacation package via Travelocity?
Travel should be about making cherished new memories and forgetting all your worries — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of getaway packages. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.
Will I save money on my Cumberland County car rental if I combine it with a hotel or flight?
Bundling your bookings into a Cumberland County vacation package will certainly save you money. You can book a car and flight; a car, flight and hotel; or a hotel and car. You won't find a better way to discover the greater Cumberland County region than with your own set of wheels. You can also add experiences and tours to your Travelocity package.
Which airport is best for Cumberland County?
Take your pick of Portland Intl. Jetport Airport (PWM) or Augusta State Airport (AUG). They are the main airports for those traveling to and from Cumberland County.
What is there to do in Cumberland County?
Cumberland County has hidden surprises around every corner, however ensure you get to Portland Museum of Art and University of Southern Maine while you're in town. These two attractions are very popular with visitors to the region.

Where to stay in Cumberland County: Best areas for travelers

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